VP of Sales, Retail Solutions

Overview

VP of Sales, Retail Solutions is responsible for leading and scaling Pomeroy's retail vertical, driving profitable growth across existing accounts and new logo acquisition. This leader will own a $114M business, with accountability for revenue performance, pipeline health, and expanding the adoption of higher-value services including Managed Services, Advisory & Consulting Services (ACS), and Smart Desk.

This is a build-while-running role
-inheriting an established team while elevating performance, strengthening sales discipline, and expanding beyond transactional selling into strategic, outcome-based solutions.

• Own and deliver $114M revenue target across the retail vertical
• Drive a 70/30 balance of existing account growth and net new logo acquisition
• Lead the shift toward higher-value offerings with a 25%+ attach rate across Managed Services, ACS, and Smart Desk
• Ensure consistent pipeline coverage of 3-4x quota to support predictable growth

• Lead a team of 8 sellers (growing to ~10), with full accountability for performance, hiring, and development
• Execute a "rebuild while running" strategy-upgrade talent, elevate expectations, and drive accountability
• Establish a high-performance culture grounded in:
  • Pipeline creation
  • Activity discipline
  • Win rates and deal quality
• Conduct 90-day performance assessments and take decisive action where needed

• Own and execute the retail vertical strategy, with a focus on enterprise and mid-market accounts, particularly within grocery and large retail segments
• Drive both named account growth and net new prospecting
• Partner with Marketing to lead account-based marketing (ABM) and targeted pipeline generation efforts
• Build industry presence through events, partnerships, and vertical plays

• Act as an executive sponsor across key accounts
• Lead deal strategy, pricing, and solution shaping to maximize margin and long-term value
• Expand relationships beyond product and professional services into strategic, multi-year service engagements

• Partner closely with Services leadership to improve alignment and drive growth in services-led solutions
• Leverage shared Solution Architects and dedicated product resources to build differentiated solutions
• Collaborate with Sales, Marketing, and Delivery to ensure alignment across the full customer lifecycle

• Predictable, scalable growth with strong pipeline coverage (3-4x)
• Measurable expansion of Managed Services, ACS, and Smart Desk across the retail base
• Improved win rates and larger, more strategic deal sizes
• Upgraded team performance with clear accountability and consistent execution
• Strong alignment across Sales, Services, and Marketing

• Bachelor's degree required.
• 10-15+ years of proven sales leadership experience in IT services and solutions, with deep exposure to the retail vertical (preferably grocery)
• Track record of leading enterprise and mid-market teams
• Demonstrated success in:
  • Growing and protecting existing revenue
  • Winning new logos
  • Expanding into higher-value, services-led engagements

• Builder mindset—comfortable transforming teams while delivering results
• Strong operator—drives pipeline discipline, forecasting rigor, and execution cadence
• Commercial leader—skilled in deal shaping, pricing, and complex negotiations
• Customer-first mindset with ability to engage at the executive level

• Ability to:
  • Protect and grow the existing base
  • Prospect and win new business
  • Expand and cross-sell strategic services beyond transactional deals
  • Experience building or upgrading teams in a performance-driven environment
  • Strong hunting orientation combined with strategic account leadership